A Night To Forget
by lsr188
Summary: When people told her that she'll never forget her first time with the person she loves, Gabriella surely didn't think this is what they meant. TxG ONESHOT co-written with LongHardRoadOuttaHell
1. Chapter 1

**AN: So Stacey and me were talking tonight and decided to do something that we've never seen on FF in the M rated fic section. An awkward sex one shot. This is purely for comedy purposes and would never wish this on our worst enemy. So please enjoy and let us know what you think.**

A Night To Forget

As Troy opened the door for me I took a deep breath before sliding in. Tonight was the night, I was no longer going to have a virgin boyfriend. We decided to do the cliché thing and finally do the _deed_ after prom. I watched as Troy slowly made his way to the driver side and unlocking the door before getting in.

"You ready babe?" His voice shook as what I presumed as nerves took over.

"Yeah." I laid back in the seat staring out the window as he pulled out of the parking lot and headed to the hotel. A part of me was twitching in anticipation and a part of me was completely mortified, but decided that this was what I wanted and I wasn't going to let anything stop me. It was going to be the perfect ending to a perfect night. About 20 minutes later I felt the car come to a stop. I look around and noticed that we were parked outside the hotel and Troy was waiting for me to get out. Pushing the door open and gathering my dress in my hands I got out slamming the door to make sure it was securely shut, well that's what I told Troy anyways. Making our way inside Troy walked ahead to check us in at the desk. I stood there feeling awkward as the girl behind the counter gave me a knowing look. Not too long after I felt Troy's hand encasing mine as he pulled me towards the elevator. As soon as the elevator doors closed my back was against a side wall with Troy's face inches from mine. I could feel his breath on my face as I looked into his blue eyes.

"Hey," he whispered, pushing a few strands of hair from my face as he lowered his mouth to mine, catching my lips in a hurried kiss, eager to start the night. Becoming mindless as his lips traveled down my neck, I slid my fingers through his chestnut hair with one hand while I reached out to steady myself with the other, jumping as the sound of an alarm went off.

Troy chuckled as he viewed my probably panicked expression and said, "I know I have the hottest girl pinned against the wall here but you don't need to bring in the Calvary. I don't like sharing."

I rolled my eyes as I quickly turned off the alarm that started the elevator in motion again.

As his hand slid up my side to gently cup my breast the elevator dinged, we broke apart thinking we had reached our floor, but instead an elderly couple stood, waiting for us to move to the side so they could enter.

Troy coughed nervously as he moved his hand away, instead taking my hand in his as we turned identical shades of red at the elderly couple's shock towards our PDA.

After what felt like an eternity under their gaze we were finally at our floor and my nerves settled back in, causing me to trip over my own feet and almost land on my face. Luckily Troy caught me and helped me back to my feet, causing me to blush even more. I was hoping this awkwardness wasn't a foreshadowing of our night together.

We reached the door of our room and Troy held up the key, brandishing it like a prized trophy, before putting it in the lock and turning it, groaning as the little red light glowed. Troy tried a few more times, sliding the keycard in and out, groaning even more loudly as he gave up.

A head of a man down the hall poked out of his room to glare at us before he shouted, "If you want to fuck your girl's brains out on what appears to be the night of your prom, what a cliché way to go by the way buddy, go do it in your own fucking room! People are trying to sleep here!"

The slamming of the door left Troy speechless while I remained mortified by his side, definitely losing some desire to do this. My thoughts were interrupted though when I heard the click of the door opening finally which set my heart racing again as I realized that the big moment was about to happen, ready or not. Troy gestured for me to go in first and I did so, setting my bag on the floor before turning back to him, waiting for him to close the door before I took a few steps forward before leaping towards him, attaching my lips to his before he stumbled back with my force and hit his head on the door, hard.

"Shit!" He called out, covering the back of his head with his hands as my mouth dropped open.

"Oh I'm so sorry Troy." I leaned over him to see if he was ok. He brought his head up faster than I could move and managed to slam his head into my nose.

"AHH!" I screamed holding my nose as my eyes began to water.

"Are you ok?" Troy asked through clenched teeth as he rubbed his head.

I nodded my head, "Yeah I'm just going to go clean up." A nasally voice escaped my lips that sounded nothing remotely close to mine. I walked in the bathroom taking my hands away from my nose to see blood running out of it. I quickly ran water over my hands and grabbed some toilet paper and rolled it up before stick it in my nose. I took the rest to gently wipe away the blood. Without a second glance at my reflection I turned and walked out of the bathroom to see Troy sitting on the bed.

"How's your head?" I asked in the same nasally voice as before.

"Sore," Troy offered. "The nose? Nice toilet paper by the way."

My hand flew up to my nose as I remembered the paper I had put up there less than a minute before, cringing I turned back to the bathroom, removing the toilet paper once I was inside and tossing it into the toilet, glad it was only a small nose bleed that seemed to have stopped now.

This time I checked my reflection before going out to Troy, making sure I didn't have any blood on my face or anything else that could potentially ruin the moment.

Walking back into the room I saw that Troy had kicked off his shoes, leaving them in the middle of the room and I couldn't help but pick them up and move them to by the door, taking off my own and leaving them next to his before I returned to the bed, setting myself down carefully as to avoid any more accidents.

In record time we were down to our underwear, my dress and Troy's tux forgotten and crumpled on the floor as hands and mouths roamed. I could feel Troy's hand on my back, inching its way up to my bra clasp and I waited eagerly for him to unclasp it, but it wasn't happening.

Troy's other hand joined his first and I shifted myself to try to give him easier access, but to no avail. Troy's inexperience and nervousness was making the simple task of getting me naked a great feat that he couldn't achieve.

Finally I sat up, turning around so my back was facing him and he had the clasp undone instantly, muttering under his breath about how pointless a bra was anyways.

Throwing the offending item to the side of the bed to join the rest of our clothes Troy pulled me back down to be laying on my side, facing him and I looped an arm around his neck as he drew me in for another kiss. Feeling a boost of confidence I slid my hand down from his neck, down his chest and his stomach until I reached the ever popular trail of hair that dipped down into his boxers.

Like Hansel and Gretel finding their way home with breadcrumbs I slid my hand down the trail of hair, under the waistband of his boxers until I was holding the prize in my hand. Eagerly I wrapped my hand around the base, pumping him as I had a few times before but at a faster pace due to my excitement.

"Ow! Gabi!" Troy called out and I realized that not only was I pumping him faster but my grip had tightened to match.

"Sorry," I replied bashfully, letting go completely and removing my hand from his boxers, returning it to his shoulder and letting him kiss me again.

His hands wandered this time, stopping to briefly caress and squeeze my breasts before he continued down to my panties, slipping a finger inside of my wetness, causing me to let out a loud moan to which he looked thoroughly shocked at.

I managed to think enough to remove Troy's boxers from his body and he followed by removing his finger from inside me, much to my disappointment and ridding my body of her panties, leaving us naked and ready for action.

Troy flipped himself so he was hovering over me and he lined himself up with my entrance, but just as he was about to take the plunge I cried out for him to stop, reminding him he needed to put on a condom.

With a sigh Troy got up from the bed and being very aware of his naked state he searched for his pants on the floor amongst the clothes. Locating them he pulled his wallet out of the back pocket and opened it up, reaching inside for the condom he had stashed in there specially for tonight.

But there was no condom inside.

"Fuck you Chad," he muttered, remembering when Chad had taken his wallet to borrow some money to put gas in his car, he'd obviously taken the condom so he could get laid tonight as well.

"What's wrong Troy?" I asked, a worried expression on my face.

"Chad stole the fucking condom," Troy groaned, tossing the wallet to the floor, feeling himself losing his erection as he realized we weren't going to be able to have sex tonight.

I racked my brain, trying to think of a way around this when I remembered the condom I had found in my bag, planted by Chad as a joke, I was sure I hadn't thrown it out.

"Go and get my bag?" I asked Troy.

"What? Why? Are you leaving?" He stammered.

"No, I think I have a condom in my bag," I replied. "Go get it."

"But I'm naked," He protested. "You get it."

"I'm naked too, and it's your penis," I shrugged, satisfied that I had won the argument.

Defeated Troy got up and crossed the room to my bag, returning to the bed holding it over himself as a covering for his growing limp manhood.

I quickly fished around inside, finding the condom and handing it to Troy who looked down at his crotch.

"I can't put it on when I'm...soft," He remarked.

With a soft giggle I bent down, taking it in my mouth and started to suck on it gently, bobbing my head up and down as I did so.

I felt Troy growing in my mouth and suddenly he jerked his hips upwards, gagging me and making me cough and splutter as I quickly moved my mouth away from him, throwing him an evil look.

"You're not meant to choke your girlfriend before you know, have sex with her," I half teased.

Troy smirked at me and ripped open the foil, fumbling with putting the condom on but getting it right in the end.

We lay back on the bed and Troy spread my legs, setting himself up once more. I held my breath as he started to move forward and let out a yelp of pain as I realized he wasn't positioned right and was missing.

"Not there, Troy," I cried out.

"Sorry," Troy replied sheepishly, realigning himself, trying to look where he was going at the same time. But he still wasn't in the right place and I yelped again as he stabbed me in my most intimate area.

After a few more failed attempts I decided to use my hand to guide him and finally his tip was just inside me, taking another deep breath he plunged into me, I tried to suppress a moan but it managed to slip past my lips as I tossed my head back into the pillow at the sensation. I kept my eyes closed waiting for Troy to move. When I didn't feel him move after a few moments I opened my eyes to see Troy's shocked face.

"You aren't a virgin?" he managed to squeak out.

I felt myself get red in the face, "I thought you knew that." At this point I seriously wanted to crawl under a rock and die.

"I know a lot of things about you Gabriella, but this sure as hell wasn't one of them"

I thought on how to make things better but the only thing to come to mind was to move my hips. As I started rocking my hips back and forth Troy suddenly groaned as his head fell onto my shoulder. Getting the idea he started to move slowly out of me and then finally back in, going far too slow for my liking.

"God Troy, I'm not a fucking doll, you're not going to break me!" I complained.

Troy seemed to get the message and started to thrust into me harder, my hips reaching up to meet his. I could feel my orgasm approaching quickly but just before I got to the edge Troy let out a strangled moan and his body went rigid for a second before he collapsed onto his forearms above me.

Through my strangled breathing I managed to form a sentence, the one sentence that said it all, "You've got to be fucking kidding me."


	2. AN

i doubt any of you remember me haha but i've been debating on coming back but under a new account, walkingproof. it already has a story posted on the account but i truly miss writing and i miss everyone i met here, i just thought i would check to see if i came back who all would be interested in reading my stories. Miss you guys! Let me know(:


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